“We competed to see who could play harder, then show up for work and still kick ass,” Rob Lowe tells Vanity Fair contributing editor Vanessa Grigoriadis about filming Masquerade in the Hamptons in 1987 while his then buddy, Charlie Sheen, was filming Wall Street. “The verdict: Charlie by a nose.” Lowe tells Grigoriadis that his friends growing up in Malibu pre-fame were the “uncool” guys who didn’t surf: Chris Penn and Charlie Sheen. “The cool girls in Malibu had no time for me,” Lowe says. “I wasn’t a beach volleyball player, a surfer, or a quasi-burnout.” However, as Lowe recounts in a Vanity Fair excerpt from his upcoming autobiography, it would be a mere five years after plotting their acting careers in the Sheens’ pool that the actor and his friends would be shot to fame.

Grigroriadis writes that Lowe “wasn’t embarrassed to admit that he began landing the cool girls,” which the actor confessed over the years included Demi Moore, Nastassja Kinski, Princess Stéphanie—who, Lowe remembers “with a fair amount of residual pride,” had a poster of him—and Washington secretary Fawn Hall, whom Lowe tracked down after seeing her at the Oliver North trial.

In his book, Lowe writes that Sheen in his early years was “one-of-a-kind … a Polo preppy clotheshorse in a world of O.P. shorts and surf T-shirts” and “a wonderful mix of nerd … and rebel.” “At my house we are still saving money by not buying desserts,” Lowe says, comparing his life to that of the Sheens, who lived nearby. “At Charlie’s house, it’s never-ending Häagen-Dazs, brand-new BMWs, a lagoon pool with underwater tunnels, and a lit, professional-grade basketball half-court.”

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During the first round of auditions in Los Angeles, Lowe writes of meeting Tom Cruise, then a houseguest of the Sheens: “He’s open, friendly, funny, and has an almost robotic, bloodless focus and an intensity that I’ve never encountered before.” In New York for the second round of auditions, Lowe finds that Cruise is “already showing traits that will make him famous; he’s zeroed in like a laser.” “We check into the Plaza Hotel. I am taken aback at the luxury and spectacle of the lobby…. The front desk tells us we will be sharing rooms,” Lowe writes of the actors’ arrival in the Big Apple. “In a flash, Cruise is on the phone to his agent, Paula Wagner. ‘Paula, they are making us share,’ he says…. The rest of us are staggering around like happy goofs….. ‘O.K., then. Thank you very much,’ he says like a 50-year-old businessman getting off the phone with his stockbroker. ‘Paula says it’s fine.’ ”

Lowe remembers hanging out with Cruise and the other actors in a gymnasium on set, when Patrick Swayze—who, Lowe writes, “makes Tom Cruise look lobotomized”—“begins to teach us a standing backflip…. When it comes to flips, I’m a pussy. I don’t flip. I don’t even dive into a pool—straight cannonball for me…. No, thanks. Cruise, not surprisingly, is all over it. ‘How about this!’ he says, almost pulling it off without even being spotted. He wipes out, but tries it again immediately.”

Lowe describes the other young actors of The Outsiders, most of whom would later become major names in Hollywood. Patrick Swayze is “as cool as you want, wearing tight jeans and a tattered, sleeveless Harley-Davidson T-shirt revealing his massive, ripped arms. (This is his uniform, he never changes it, and if I looked like him, neither would I.),” Lowe writes. In Vanity Fair’s excerpt, Lowe goes on to describe his Outsiders co-star Matt Dillon as a young ladies’ man—picking up an ogling young fan in the hotel’s lobby; pins Diane Lane as everyone’s set crush (“At only 16, she already seems like a legend.… I watch as she breezes by with her chaperone. With all the teen testosterone on this movie, she’ll need one!”); and recalls how director Francis Ford Coppola had all the actors perform Tai Chi during rehearsal (“How does a 60s greaser know or care about Tai Chi? But if the world’s greatest living director thinks we should stand on our heads to prepare, we should probably do it”).

Lowe tells Grigoriadis that despite a rocky patch following his 80s stardom that landed him in rehab, he has no regrets. “The Brat Pack is timeless,” Lowe says. “We should all be so lucky in our lives to create things that we’re still talking about 25 years later.”